Cyclohexyl radicals, generated by decomposition of dibenzoyl peroxide in cyclohexane, add to 2-(2-phenylethynyl)phenyl isothiocyanate to afford thioimidoyl radicals. Despite the unfavorable fragmentation equilibrium, these radicals give rise to a multi-step cyclization/H-translocation process yielding a spiranic polycondensed heterocyclic compound. An analogous spiranic dihydro-derivative is obtained from reaction of the corresponding alkynyl isonitrile with cyclohexanethiol under radical conditions.
Multi-step radical spiro-cyclization of an alkynylaryl isothiocyanate
MINOZZI, MATTEO;NANNI, DANIELE;ZANARDI, GIUSEPPE;
2006
Abstract
Cyclohexyl radicals, generated by decomposition of dibenzoyl peroxide in cyclohexane, add to 2-(2-phenylethynyl)phenyl isothiocyanate to afford thioimidoyl radicals. Despite the unfavorable fragmentation equilibrium, these radicals give rise to a multi-step cyclization/H-translocation process yielding a spiranic polycondensed heterocyclic compound. An analogous spiranic dihydro-derivative is obtained from reaction of the corresponding alkynyl isonitrile with cyclohexanethiol under radical conditions.File in questo prodotto:
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